Sodium Hydroxide → HCID 15067997, compound

HRID 1074283Notes

Reaction equation

HRID 1074283 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24].[OH-].[Na+]>CN(C)C=O>[C:11]([C:9]1[CH:8]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1)[O:15][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 708253,5-Di-tert-butylphenolHCID 88737Heptanenitrile, 7-bromo-

Product 1

HCID 15067997HCID 15067997, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture containing 20.6 g (0.10 mole) of 3,5-di-t-butylphenol, 20.9 g (0.11 mole) of 7-bromoheptanenitrile, 4.0 g (0.10 mole) of sodium hydroxide and 250 ml of dimethylformamide was heated at 120° C. for about forty hours. The solvent was evaporated and the residue was added to 250 ml of water. The resulting oil was separated and dissolved in 250 ml of diethyl ether. The ether solution was washed twice with 250 ml portions of 10% sodium hydroxide, washed once with 250 ml water, dried over magnesium sulfate, and evaporated to give an oil which solidified on standing. The solid was recrystallized twice from methanol. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was added to 250 ml of water
  3. customThe resulting oil was separated
  4. dissolutiondissolved in 250 ml of diethyl ether
  5. washThe ether solution was washed twice with 250 ml portions of 10% sodium hydroxide
  6. washwashed once with 250 ml water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customto give an oil which
  10. customThe solid was recrystallized twice from methanol

Sources & evidence

ORD record
ord-e32e41fd8d154645b6d308e5c0bde38f
Source dataset
uspto-grants-1990_11
Patent number
US04973731

Reaction notes

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